Healthcare as we know it is in the process of going through a massive change - from episodic to continuous, from disease focused to wellness and quality of life focused, from clinic centric to anywhere a patient is, from clinician controlled to patient empowered, and from being driven by limited data to 360-degree, multimodal personal-public-population physical-cybersocial big data driven. While ability to create and capture data is already here, the upcoming innovations will be in converting this big data into smart data through contextual and personalized processing such that patients and clinicians can make better decisions and take timely actions for augmented personalized health. This paper outlines current opportunities and challenges, with a focus on key AI approaches to make this a reality. The broader vision is exemplified using three ongoing applications (asthma in children, bariatric surgery, and pain management) as part of the Kno.e.sis kHealth personalized digital health initiative.